Go Off the Beaten Path in These Connecticut Villages Last Updated: April 2022

Some of Connecticut’s smaller, less well-known towns have been described as “sleepy” or “undiscovered gems.” But the people who live there, and the people who visit, know differently. These towns might be overshadowed by a larger town or city, or maybe they are not easily reached by the interstate, but they have a personality that makes visiting them worth going “off the beaten path” for. And at a time when we are all trying to keep a safe distance from one another, discovering some of the state's lesser-known destinations is a great way to do so.

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Beach Chic Branford

On the Connecticut shoreline, the town of Branford is not far from the city lights and culture of New Haven but visiting this town for a few days can give you the impression you’re in a beach town on an island somewhere. The nearby Thimble Islands offer a backdrop to all kinds of water activities. Take a cruise on the Sea Mist to get your bearings, then get out on a kayak or paddleboard yourself. Relax with a craft brew at Stony Creek Brewery or Thimble Island Brewing Company or achieve the ultimate in relaxation at By the Sea Day Spa.

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New Milford's Magic

If you have ever watched “The Gilmore Girls,” you may feel a sense of déjà vuin this western Connecticut town. Tucked away in the hills just a few miles from the New York border, the town of New Milford features a classic town square complete with gazebo, just like the one in the Gilmores’ fictional home town of Stars Hollow. Book a stay at the charming Homestead Inn, and plan a visit around a hike in Lovers Leap State Park and a trip to Housatonic River Brewing located on the scenic Housatonic River.

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Dapper Darien

Between the cities of Stamford and South Norwalk, you’ll find the town of Darien, Connecticut. Back in the day this “commuter” town established itself as home for many people commuting into New York City on the Metro North Line. It’s also home to picturesque beaches, historical homesteads and charming restaurants like Rory’s. Stay the night at the nearby Stanton House Inn and book some "me time" at the Salt Cave of Darien.

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Vintage Putnam

In Connecticut’s northeastern “quiet corner,” pretty Putnam is a 19thcentury mill town that has become an antique lover’s paradise. Start at the Antiques Marketplace and grab a bite just down Main Street at the 85 Main. Book a stay at the beautiful Mansion at Bald Hill in nearby Woodstock. And don’t miss the hot dogs, seafood and ice cream at famed Deary Brothers/Mike’s Stand.

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Colorful Collinsville

The tiny village of Collinsville, part of the town of Canton, is packed with things to do. Stay at the Old Riverton Inn in nearby Riverton so you can get an early exploring the beautiful Farmington River with Collinsville Canoe & Kayak. Spend an hour exploring an old factory now filled with antique dealers at Antiques on the Farmington and be sure to grab a bite at the Crown & Hammer Restaurant and Pub.

Explore more of Connecticut’s favorite cities, towns and villages here.